Reductive Knoevenagel Condensation with the Zn–AcOH System

Abstract

An efficient gram-scale one-pot approach to 2-substituted malonates and related structures is developed, starting from commercially available aldehydes and active methylene compounds. The technique combines Knoevenagel condensation with the reduction of the C=C bond in the resulting activated alkenes with the Zn–AcOH system. The relative ease with which the C=C bond reduction occurs can be traced to the accepting abilities of the substituents in the intermediate arylidene malonates.

Key words

electron transfer - malonate - reduction - reductive alkylation - zinc

Publication History

Received: 21 May 2020

Accepted after revision: 16 September 2020

Article published online:
29 October 2020

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